Jackie O went down in history as being one of the most fashionable First Ladies that the White House has ever seen. She remained in the spotlight for decades and didn’t seem capable of taking a bad photo. Jackie could make any trend — from pillbox hats to broaches — look effortlessly classy. Whether she was wearing elegant elbow gloves or a flashy print dress, the socialite was always camera-ready. Read on to see some of Jackie O’s most iconic looks over the years.
Her Pillbox Hats Added Charm To Any Ensemble
One fashion trend that’s emblematic of the ’50s and ’60s is the pillbox hat. Though they initially came into popularity in the ’30s, their presence in mainstream fashion was perhaps most recognizable during Jackie’s term as First Lady.
The hats added even more charm to the admirable socialite. She would style her hair so the ends flipped inward for the quintessential 1960s look. Jackie also made sure that her pillbox hats always matched her outfit perfectly.
Oversized Sunglasses Were Her Trademark
If there’s one fashion trend that Jackie unabashedly brought to prominence, it’s oversized sunglasses. Decades later, similar variations are still available in various apparel stores. Though some might say that such massive glasses offer a bug-eyed look, there’s no denying that Jackie could always pull it off.
While some of us experiment with different styles of sunglasses — from aviators to cat-eyed — Jackie primarily stuck to one variation. From her youth to her senior years, the First Lady held a “the bigger, the better” approach to sunglasses.
She Stunned In Strapless Gowns
When it was time to dress up, Jackie’s go-to was strapless gowns. The style showed off her understated beauty by letting her face and shoulders steal the show. She’d enhance the look with some brilliant earrings that stuck out all the more in the absence of straps.
Jackie was only 31 years old when she became the First Lady, making her the third-youngest in the role. Though she had an air of being beyond her years, her youth inevitably lightened up her looks.
Elbow-Length Gloves Made Her Look Like Royalty
Jackie would often pair her strapless gowns with elbow-length gloves. The accessory added tremendous class to any outfit, as it was dressier than the wrist-length gloves she would often wear while out and about.
The gloves were so lengthy that they would come up to about the same spot on her arms as her strapless dress. This would create a straight line above which her shoulders would emerge. She would even omit wearing a necklace to let her natural beauty shine.
She Wore A Boatneck Gown For Her Wedding
Jackie O was a vision on her wedding day, for which she chose a gorgeous boatneck gown. If the look seems familiar, it may be because Meghan Markle also wore a boatneck wedding dress when she said “I do” to Prince Harry.
The First Lady would continue to wear boatneck dresses long after her big day. It was among her favorite styles of dresses, which makes sense considering it’s a cousin of the strapless gown.
She Would Often Pair Headscarves With Her Sunglasses
One of Jackie’s casual but still elegant looks was headscarves and sunglasses. It was another popular look in the ’60s that Jackie made look effortlessly stylish. Even when she was just relaxing outdoors, the socialite looked like a movie star.
Jackie proved that looking glamorous wasn’t just about dressing up in jewels and fancy outfits. As the saying goes, less is more. The first lady was an excellent example of how a toned-down look can still be iconic.
Jackie Got Down To Business In Feminine Suits
In many of her public appearances related to her husband’s presidency, Jackie would be seen in outfits like this one. The professional attire consisted of a matching suit skirt and jacket, typically featuring large buttons running down one side.
The feminine suits were both form-fitting and modest, presenting Jackie as the classy professional she was. She would often wear the outfit with pearls tucked into the high collar, studded earrings, and hair styled with an exaggerated flip at the tips.
She Could Pull Off Equestrian-Inspired Outfits
Jackie started riding horses as a young girl and continued to do so into adulthood. The sport influenced her fashion and she managed to make equestrian-style outfits look just as upscale as the rest of her closet.
Though much of her style choices were quite feminine and with the times, her equestrian style gave her a more masculine and old-fashioned look that she pulled off just as well. The flowy pants and rigid shoulders would emerge in ’80s female apparel, but Jackie was ahead of the times.
She Made Capes Classy
If you thought it was impressive that Jackie could bring the equestrian look into fashion, just look at how she sported capes. When we think of capes, we tend to think of Dracula, not an impeccably stylish First Lady.
She managed to make a cape look like the classiest part of her outfit. Jackie wasn’t afraid to go big when it came to her fashion. She’s even reported to have spent 150% of her husband’s presidential salary on fashion.
Her Hair Was Always Styled In A Bouffant
When Jackie wasn’t wearing hats or headscarves, she was showing off her impressively voluminous hair. She styled her hair the same way the entire time she was First Lady: jaw-length with side bangs and a bouffant.
Bouffants consist of puffed-up hair shaped into a round shape. You never saw Jackie’s hair fall flat. The person behind her flawless hair was Mr. Kenneth, a top hairdresser in New York whom actresses Audrey Hepburn and Marilyn Monroe also visited.
Sheath Dresses Were A Staple For Jackie
One of the staples in Jackie O’s closet was the sheath dress. They are characterized by being straight cut and form-fitting, streamlined, and hitting just at or above the knee.
They often have subtle patterns and short sleeves. In Jackie’s case, she most often wore sheath dresses that came up to her neck and bared her shoulders. She loves both vibrant and pastel colors. One of her favorite colors to dress in, be it casual or dressy, was pink.
Her Outfits Often Featured Bows
Jackie knew how to make bows look grown-up. This black sheath dress features a slender bow that rests at her waistline and matches her white gloves. At times like these, Jackie’s style almost looked like it was modeled after a wealthy young woman.
We could see her younger self wearing a modest dress like this one with bows in her flipped hair. Jackie heightened the innocent look with pearls and gloves, making it something women of all ages could model their style after.
She Liked To Match With Her Kids
These days, social media moms love showing off outfits that match with their children’s. Long before the days of internet trends, Jackie was dressing up her kids so they would match her while out in the public eye.
Here she is walking with John Jr., wearing a short-sleeved black t-shirt that matches her son’s long-sleeved shirt. They are also both wearing sand-colored khakis. Jackie didn’t go overboard on matching with her kids, though, as is apparent by the pink-clad Caroline in the background.
She Wasn’t Afraid To Wear All-White
Jackie’s wedding day wasn’t the only time she appeared in all-white. The first lady loved to dress in white outfits like this one. She wasn’t afraid of doing white on white-on-white, such as this dress with matching gloves and a hat.
She once went sailing wearing white pants, a white top, a white headscarf, and white shoes. While many can’t imagine doing something outdoorsy while wearing such a stainable outfit, but Jackie didn’t mind.
She Made Broaches Seem Hip
Broaches may seem like they’re reserved for grandmothers, but Jackie made the accessory seem perfectly acceptable for a young person to wear. In this photo, her rose broach brings a pop of color and design to her all-black outfit.
While we’re at it, let’s take a moment to appreciate the fact that Jackie is in all black. She wasn’t headed to a funeral, but rather enjoyed wearing one solid color. As with her all-white outfits, she makes the solid black ensemble look far from boring.
She Popped In Print Dresses
Once the ’70s came along, it was all about funky styles and bold prints. Jackie adjusted her style to boast more playful outfits that strayed from her professional looks but kept all the class.
Here she is wearing a print dress with a unique design that stands out. It’s also a shift dress, which is similar but looser than her former sheaths. She stayed true to her love of pearls, but opted for a long necklace instead of the short ones she doted as First Lady.
She Loved Loud Belts
Though Jackie was the queen of simplicity, she did like to incorporate flashy accessories that would make a statement, like this gilded belt. Her long-sleeved dress is loose and simple, balancing out the loud belt, which gives the outfit shape and pizzazz.
Her earrings match the belt and bring attention back to her face. Jackie’s hair is in her usual bouffant style, only this time her bangs are pulled back to give her a more regal look.
Jackie Knew How To Make Casual Look Chic
Even when Jackie dressed casually, she still looked like she was ready for a photo shoot. This younger photo of the socialite shows her in a button-up tucked into high-rise shorts and wearing a straw hat.
Years later, she would have the same flair for making simple outfits seems extraordinary. From khaki skirts with matching jackets to flowy, polka dot dresses, Jackie had an eye for picking out everyday clothes that still set her apart in a crowd.
She Knew How To Make Turtlenecks Look Good
Turtlenecks don’t have the best reputation with many women, primarily because they can be unflattering. Fashionista Jackie wore her turtlenecks proudly and looked great doing so. She would often pair them with a jacket and slacks.
The simplicity of turtlenecks went hand-in-hand with Jackie’s subtle yet elegant style. Though turtlenecks aren’t exactly glamorous, the first lady somehow made them seem like an integral part of any wardrobe. Sometimes you just need something to easily throw on, and for Jackie, turtlenecks were about as basic as she went.
Coats And Jackets Completed Her Ensembles
Have you ever put on the perfect outfit and then dug through your jackets looking for one that would match? For Jackie, her outfit wasn’t complete unless she had a coat or jacket that matched just right with the ensemble.
You wouldn’t see her wearing a jacket that she picked out of the coat closet last minute and just threw on. Like her purses, she had just the right jacket or coat for every outfit.
She Knew How To Strike A Balance Between Casual And Classy
Here’s Jackie O at the New York Harbor, where she had just arrived from Staten Island. Being near the water one a windy day would call for something more casual to wear, but Jackie knew how to still keep it classy.
She went with a black blouse tucked into white pants and lefts a few buttons open to reveal her white camisole underneath. She paired the outfit with a simple necklace and a watch to add understated glam to the ensemble.
She Looked Charming As Ever At Kennedy’s Memorial
Even while attending the inauguration of a memorial to her husband, Jackie looked charming as ever. She chose an outfit that the public knew her best in: a skirt suit with a pillbox hat.
The light color of the outfit gave her a bright air on an otherwise heavy day. Her hair was styled in a bouffant at her bangs with a flip at the ends. Given the circumstances, Jackie wowed with her admirable grace and subtle strength.
Jackie’s Classic Georgetown Photoshoot
When Jackie posed in her Georgetown home, she introduced the public to her timeless style. She wore a pink shift dress with pearls and a bouffant hairdo, all of which would become part of her signature style.
The first lady had a way of coming across equally friendly and sophisticated. Though she undoubtedly was elegant and lovely, she also seemed approachable. It’s no wonder she’s still regarded as one of the more popular first ladies in American history.
Still Showcasing White Gloves
When Jackie planned the outfit she would wear at her daughter, Caroline’s, wedding in 1986, she was sure that white gloves were part of the ensemble. Though she adopted a more casual style after her days as the first lady, her early fashion trends remained a part of her later in life.
The occasion was the perfect time for Jackie to showcase how she’s elevated her style. Her flowy dress is reminiscent of her pastel sheath dress from decades prior, as are her earrings, gloves, and that bouffant hairstyle.
Her Style Changed With The Times
Though Jackie almost exclusively wore dresses and skirts while in the white house, she met the ’70s with a more laid-back style. Here she is walking down the street in New York wearing a casual pantsuit.
She’s traded in her short necklaces for a long and flowing one that is reminiscent of her pearls, but has more of a jazzy feel. Her shiny bracelets are another emblem of the era. The year was 1970, and Jackie was as trendy as ever.
Her Early Style Was Posher
When you think of how a woman’s style would transform over the years, you may think that it would get posher over time. For Jackie, it was the reverse. This early modeling image shows how professionally she would dress in her early years.
Here she wears a black, elbow-length blouse that meets her choker pearls. She has white gloves, a broach, and a subtle, silver bracelet. Jackie presented herself as being serious and modest early on, but her style became more loose and casual as she aged.
She Wasn’t Afraid To Mix Bold Colors
Jackie was one of those fashion gurus who could make just about any outfit look like it was a statement. Here she is at a pier wearing a bright blue long sleeve with a matching headscarf.
Her pants are a green-yellow that you may not have thought to pair with the outfit, but Jackie makes it look like the perfect summer ensemble. Like a true model, she could pull off just about any look, and the bright colors somehow complement one another.
She Had A Keen Sense Of How To Pair Things
This is another example of Jackie pairing clothing items that wouldn’t be immediately obvious as an ensemble. She topped her green-brown turtleneck with a white jacket with gold embellishments.
Over her head is a light grey scarf and on her arm is a light brown and off white purse. Separately, many people wouldn’t have thought to grab all these items, but they somehow come together without clashing. After decades in fashion, Jackie had developed a keen sense of style.
A Funky Belt And Pants
Jackie was doing some shopping out on the town when someone snapped this photo of her. Long past her White House days, she looked laid back in her simple tee shirt and felt pants with a leopard-like print on them.
She completed the outfit with a circular belt that’s just for looks, almost like a necklace for her hips. Jackie echoed the round patterns in her hoop earrings, an accessory very indicative of the times.
Her Fancier Outfits Also Transformed In The ’70s
Jackie didn’t only transform her casual attire in the ’70s, but also her dressy looks. Here she is arriving at a restaurant wearing a flowy, red dress with sheer sleeves and ruffles at the chest, waist, wrists, and shins.
A golden tie cinches her waist and makes the ensemble look like it could be for the holidays. Where her former dresses were often sleek and made of a heavy fabric, this one has a more fun-loving tone.
Jackie Could Make Fancy Look Effortless
Here’s Jackie looking out at the horizon while posing with John and their daughter. She’s wearing a pink dress that has a very small and subtle plaid design with a pearl necklace, as usual.
This gown is a little fancier than her shift dresses and it flares out at the hips, almost like a ballgown. Even so, Jackie makes it look casual as she sits on a fence in front of the countryside.
Her Hair Also Changed With The Times
Not only did Jackie’s fashion transform over the years, but so did her hair. The first lady often kept her locks at or above her shoulders and would flip them inward or out at the ends.
Here, Jackie is at an airport in the ’70s and is wearing her hair combed back, long, and wavy. Though she still has a slight bouffant up top, it is pulled back and hangs long like you might expect one of the movie stars at the time to style their locks.
Her Outfits Always Had Some Small Embellishment
Here Jackie O is about to leave to have lunch with Queen Elizabeth II. Such an honor puts added pressure on what one should wear, but Jackie went with something simple yet elegant.
Her skirt suit would be completely plain if not for the single button in the center and the broach on her shoulder. Jackie’s ensembles were never boring because they always had a subtle embellishment, even during extremely professional meetings as this one.
She Looked Radiant At The Airport
Airports may be the furthest thing from a fashion show, but Jackie still dressed like she was headed to Paris Week. Here she is accompanying her second husband to his plane while dressed in a white jacket and matching miniskirt.
Mind you, miniskirts back then were anything above the knee, something you’d never see Jackie in prior to the ’70s. As we mentioned before, her style became younger and younger as she aged, which also had to do with the fashion evolution of the times.
Her Dress-Length Coat
Jackie always seemed to have whatever she needed to complete her ensemble. In this case, it was a coat that went the same length as her dress. The coat features large buttons — a Jackie favorite — and a subtle plaid design made more professional looking by a collar.
Even as Jackie fixes her windswept hair, she looks elegant. She truly could not take a bad photo. She also didn’t seem to mind always having eyes on her.
With The Family
Here the Kennedy family is getting ready to head out for Easter Sunday in Miami, Florida. Given Jackie’s fashion sense, we would be willing to bet that she coordinated all of their outfits.
John is in his usual black suit, while the children match their mother wearing all white, similar-looking outfits. Jackie completed her look with white gloves and a white headscarf, two of her favorite accessories. As we previously mentioned, Jackie had a flair for matching with her children.
Wearing A Scarf Like A Tie
By now, it should be no surprise that Jackie had a plethora of scarves. However, it wasn’t until the ’70s that she began wearing them like a tie, as she is in this image of her leaving the Philharmonic.
Her high-collar white button-up and matching black jacket and trousers are like a feminine version of the suits her late husband so often wore. Jackie’s hair is also longer and more curled than we would have previously seen it.
Combining Some Of Her Favorite Trends
Multiple trends that Jackie favored are apparent in this outfit, which she wore to attend a dinner with the Prime Minister of Japan at the Japanese Embassy. The top of her dress hugs her like a sheath dress and has the boat neckline that her wedding dress had.
At her cinched waist is a bow, and her white gloves extend past her elbows. The bottom of the shiny dress isn’t flowy, but is rather an extension of the fabric used above.
A Somber Look
When Jackie attended the funeral of Cardinal Cushing, she went with an outfit that was similar to the dress suits she wore in the White House, but a little more homey-looking.
The primary difference is in the fabric, which in this case is knitted and has subtle fringe embellishments. She also wore black lace in her hair and black gloves to match the rest of the ensemble. Jackie’s hair is straight and flips out at the ends.
Jackie Loved Eye-Catching Patterns
Though Jackie’s single-colored outfits of her early days may have you believing she favored simplicity, she proved in later years that she wasn’t afraid to be flashy. This black and white zigzag dress is a perfect example.
Jackie let her love for eye-catching patterns blossom in the ’70s. Here she is leaving a theatre in New York. While she may have dressed more professionally for the occasion in the past, she now had more freedom in terms of her style.